Lesbian 101: Rules for a One-Night Stand

Today, we’re going to discuss one-night stands. Let me preface my remarks by making clear that what I’m about to tell you is not a moral indictment. Rather, it is a bit of wisdom earned from some very long nights spent with some very sad strangers.

That said, here’s my first piece of advice: Avoid one-night stands. They are no fun.

Another note: This advice applies to lesbians only. From what I understand, gay men have mastered the art of impersonal sex, and I salute them.

Before you march over to your computer to type out an angry rebuttal, I want you to take an honest assessment of your sexual past.

Ask yourself these questions:

• After a one-night stand, have you ever skipped down the street (still wearing the clothes you were wearing the night before), happily telling yourself, “Oooh, I just can’t wait to have sex with a stranger again!”

• Was the sex you engaged in anything other than awkward, confusing, and kind of icky? Did it leave you with the same emptiness you feel after eating fast food?

• Did one of the two women involved break out in tears at some point, bemoaning the recent loss of a cheating girlfriend?

• Did your initial feelings for this stranger (lustful) deepen into something more meaningful (affectionate) or sour (regret or disgust) following the encounter?

Considering that every lesbian I know is either in a relationship or longing to be in one, I suspect 99.9 percent of all lesbians have had a pretty miserable history with one-night stands.

Here’s the biggest problem with one-night stands: Women rarely enter a sexual encounter thinking it will be a one-time thing. We don’t determine that it has a limited shelf life until we’re well into the fumbling sex.

So, disappointment is inherent in the one-night-stand. We either (a) Want the stranger to fall in love with us; or (b) Want to fall in love with the stranger, and when that doesn’t happen it’s upsetting.

But, we never learn from our mistakes, and we’re going to keep having one-night stands.

So, here are a few rules that will enable you to handle them with grace, dignity, and a bit of fun.

(1) Insist on spending the night at her place, so you can make a quick escape the next morning.

(2) Do not cry at any point during the encounter.

(3) Keep the sex simple. Don’t try any fancy stuff. You don’t know what she likes, she doesn’t know what you like, and you’ve got only one night to figure it out. So, stick to the basics.

(4) I don’t care how drunk you are, do not invite her to have breakfast the next morning with your parents.

(5) Do not fall into a relationship with her pets.

(6) Do not feel bad about yourself the next day. Giggle at your naughtiness. And don’t forget to take a hot, cleansing bath.

(7) The next day, call all your friends who are in relationships, and tell them about your encounter. They’ll act outraged, but actually will be pea green with envy.

(8) Give her a call in a few days, and tell her that you had a nice time, but make no plans to meet. This simple courtesy will make you each reevaluate the disappointing evening, and allow you to greet each other with real affection when you bump into each other again. Then, you can share a giggle over your naughtiness, but don’t sleep with her again. Remember: “One-night” has a well-defined expiration date.


Hey! I wrote a book. You can buy Dateland on www.amazon.com.

5 Responses to Lesbian 101: Rules for a One-Night Stand

  1. *sheila says:

    OMG, yes i’m feel all f*cked up after a recent 2 night affair with a lady i met one night. She was my first person that i’ve ever had sex with, and i actually cried seeing her the 2nd time. AHHHHH hahaha/ Well she’s going away home to her country in a few days, yet my mind still wants to believe something more will grow from it. Reality checking, we had a good time, but it’s over now. Yes i’m disappointed, no regrets though.

  2. RedSonja says:

    Unless you’re completely devoid of emotions or sensitivity, your one night stand is not going to remain a one night stand. If not physically, mentally for sure AND socially. You’ll never be able to run into that person again without 1) being awkward 2) someone falling apart 3) scornful glances or 4) wanting to fuck her again — most likely not mutual. SO… don’t do it. You might think you’re a badass player but believe me, the emotional baggage will be there either from you or the other girl. We’re women… we’re not supposed to have meaningless sex! No strings sex maybe… but doesn’t have to be meaningless. Call them the next day, act the same as you did before you slept together, communicate whether or not it was a one time thing and ask how they feel about it. Don’t purposely wait 2 days just to manipulate the situation into what you want whether it be more sex or to send the message you don’t want to sleep together again.

    Be honest. That’s it.

  3. Ruby says:

    once in my teens i had a one night stand with someone 6 years older than me. she had a girlfriend studying abroad that she cheated on with me. i was the other woman! what a weird feeling! but it was a great feeling knowing that i, as a horny, hormonal teen, could rock her 5 year relationship enough to make her want me. not to mention how good the sex was! still a fond memory!

  4. m-spirit says:

    i am a seasoned gay woman and i have to agree. i just can’t enjoy the one night stand, you have to build up to knowing each sexually. i have really tried and just is not satisfying. my best advice is to cultivate a f–k buddy. this works very well – have more than one if you like.

    the rules are that you only meet for brief encounters and know that the only thing that will ever come from the relationship is HOT SEX – you have to engage a part of yourself, but a serious relationship is NOT possible. you don’t spend days or too many hours together.

    this person is not a friend really and is not going to be a close friend. choose someone you’re really sexually attracted to, but don’t like to spend too much time with. this has to be someone who you can handle for short periods of time and you both agree to these terms.

    the exchange between women is not as superficial as heterosexuals or gay men, so we have to do it in a way that addresses how a lesbian thinks and feels.

    good luck!

  5. Julie says:

    I had a one night stand yesterday with my friend. She is 25 years old, and Iam 17years old. She was straight befor i came in to her life. And she still is, i think. Its not awkward between us, actually. We have never talked so much befor all of this! And i love it

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